


All I Know Is Touch and Go

by linksofmemories



Category: Teen Wolf (TV)
Genre: 5 times + 1, Alternate Universe - Canon Divergence, Anal Fingering, Anal Sex, Bottom Stiles Stilinski, Coming Untouched, Complete Disregard for Season Three, Fisting, M/M, Masturbation, Mention of Knotting, Phone Sex, Rimming, Self-Lubrication, Top Derek Hale, Vibrators
Language: English
Status: Completed
Published: 2014-02-23
Updated: 2014-02-23
Packaged: 2018-01-13 12:09:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,573
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1225738
Author URL: https://archiveofourown.org/users/linksofmemories/pseuds/linksofmemories
Summary: <blockquote class="userstuff">
              <p>And with his fingers pressing inside of him and his cock brushing against the sheets and his face in the leather that smelled like Derek, he felt pathetic and desperate all at once. He knew that if he ever got the chance (the <em>opportunity</em>) to be with Derek that he’d ask him to fuck him within half a second. He wanted the older man inside of him and around him and all over him until his senses were so consumed that he was completely senseless.</p><p>
  <em>or</em>
</p><p>The five times Stiles fingered himself and the one time Derek did it for him.</p>
            </blockquote>





	All I Know Is Touch and Go

He was 14 and it was the summer before his freshman year and he was standing in the drugstore that was a five minute walk from his house. Scott was getting his tonsils removed and Stiles didn’t exactly have anyone else to hang out with. His dad was working and had given him the simple task of going to the store to buy toilet paper and shaving cream (and had generously allowed him to buy a candy bar with the money as well).

Stiles was currently contemplating the different brands of shaving cream (his dad had said cheap, but not too cheap) with a pack of 12 rolls of Charmin in his basket and a Reese’s. He decided on a can promising the smoothest and closest shave, but in shitty packaging, and dropped it in his basket. Stiles was about two seconds from walking to the check-out counter when he noticed the lubes and condoms two shelves over.

The condoms probably weren’t going to do him any good and would more than likely be expired when he got around to using them, but the lube looked promising. His face was practically burning as he inched toward the display, looking around the aisle to make sure no one saw him. When he jacked off it was usually using spit or the unscented lotion Ms. McCall bought for him and his dad, always lecturing that their skin would get dry and cracked if they didn’t moisturize.

Lube had always been something he wanted to try though. He had seen porn and read articles and knew that lube was the most ideal thing to use. He had also been thinking about… adding a new thing to his jerking off routine and lube seemed like the best way to do it.

So, without further ado, Stiles grabbed a bottle of standard water-based lube and practically threw it in the basket before marching to the check-out counter.

“Hi, Stiles,” the cashier, Laney, greeted. She had been working there since he could remember and she always recognized him since he was the Sheriff’s son. “Find everything okay today?”

“Yep,” he nodded, rocking back and forth as he watched her scan the toilet paper and then the shaving cream. “How’s work?”

“Same old, same old,” she shrugged, scanning the Reese’s before handing it back to him, knowing he’d want to eat it on the walk home. Laney’s hand came to the lube and her face didn’t even change, scanning it and putting it in the bag with the other purchases.

She told him his total and he gave her the $20 his dad had given him. After giving him his change and stuffing his receipt in the bag before handing it to him, she told him to have a nice day with a wink. A _wink._ Oh God, he was so screwed.

He awkwardly nodded, taking the bag before practically running out of the store. Stiles ripped open his Reese’s as he walked back to the house, munching nervously as he carried the bag that felt like a thousand pounds.

There was no reason to freak out though. This was normal. Everyone jerked off and he just wanted to add some lube to the routine. Chaffing was a bitch, anyone could get that.

Even though he kept telling himself that it was because of chaffing and not because of the… other thing. It took a lot to make Stiles embarrassed and nothing made him more embarrassed than the idea of… putting his fingers up his ass, like how was that even supposed to feel good? He got that his prostate was hiding up there somewhere, but putting his fingers where his shit came out didn’t seem that appealing.

Curse his natural curiosity.

He finished his Reese’s right as he walked up his driveway, throwing away the wrapper in the trashcan before heading inside. Stiles placed the receipt and change on the kitchen table before putting the toilet paper in the hall closet and the shaving cream in his dad’s bathroom. He checked the time, seeing that he still had two hours until his dad was home.

And that was enough time, he figured. It’d definitely be enough time if it turned out he hated it and just resorted to stroking his dick like usual. So, he shoved all his insecurities aside and grabbed his laptop, bringing up the article he had been reading before going to the drugstore. It was a very detailed and helpful how-to on the wonders of anal fingering (man that sounded so weird) and he was determined to follow it step-by-step.

First, Stiles placed a towel on his bed to make sure the lube wouldn’t get on his sheets. Then, he opened up the lube, put on some low-key indie music that he would never listen to in a situation that wasn’t this current situation, and dimmed the lights. He almost laughed, the thought of _wooing_ himself was more than a little ridiculous.

He pressed on though, taking off his clothes before lying comfortably on his bed. Stiles breathed out and closed his eyes, remembering that the article said that he should think about things that turned him on, _aroused_ him. And nothing did that better than Lydia Martin.

Lydia with her long strawberry-blonde hair and her green eyes and smooth pale skin and tiny waist and her douchebag boyfriend who would laugh at him for what he was about to do. So, no, okay, no Lydia for this. Maybe a faceless person. Girl. A faceless girl.

Or maybe not because that seemed embarrassing as well.

Stiles squirmed on the mattress, trying to think of something not completely mortifying. He grabbed the bottle of lube, uncapping it and pouring a bit on his hand. He brought it around his cock and gave a stroke before groaning, his head tilting back against his pillow. _Fuck_ , that felt so much better than doing it dry or just with his spit.

He stroked himself to hardness, his hips doing little thrusts up into his fist. The slick slide of the lube on his skin was perfect and he knew that all of his allowance would probably stop going completely to video games after this. Whenever he jerked off he never made a sound, too paranoid of his dad hearing and he found that he never really needed to make a sound. But he was home alone and it felt too good not to make a few noises.

The moans and gasps and sighs that came from his lips were completely new to him and he let them all fall out, not at all self-conscious for once in his life. Soon he was so turned on and right on the edge that he knew that it was either let himself come or start to do what he had been planning on.

He stopped his hand, glancing down at his cock to see it full and red and dripping onto his skin. After pouring more lube, this time onto his fingers, he gave a shaky sigh before spreading his legs. The first touch of his finger against his hole made his face heat up in embarrassment despite being completely alone. He fought it back though, rubbing the pad of his finger against himself until his entrance unclenched slightly, letting his finger just press inside.

Inhaling deeply, Stiles pressed the finger in further, his body slowly adjusting to the intrusion. He continued, the feeling strange more than painful. His finger was all the way inside before he moved it around, trying to think of all the tips for finding his –

“Holy _shit_ ,” he cursed, his free hand clutching the towel under him.

Okay. He had found it. He had found it and _fuck_. Never in a million years did he ever imagine it feeling that good. But maybe it was just a onetime thing or beginner’s luck or something?

Stiles tried again, curling his finger just right until he was letting out a low moan, sparks of pleasure filling him up. All he could think about was the possibility of two fingers, so he pressed another inside. The stretch more prominent, but he was too turned on for it to even hurt.

His chest was moving up and down as he curled two fingers against his prostate, his mouth falling open and his legs shaking and his cock dripping even more pre-come. He started to move the fingers in and out while taking his cock once again. There was no way he was going to last long, but at the moment he really couldn’t care.

He fucked into his fist while his fingers fucked him and _shit_ , the idea of someone fucking him. Not even with fingers. The idea of someone being inside of him and filling him up and hitting his prostate more fully and telling him that he was doing _so good_ and-

“ _Oh_ ,” he moaned as he came, coating his stomach and tightening his ass around his fingers. Stiles tilted his head back against the pillow, breathing heavily and feeling like mush.

Getting fucked. Huh. Well that was a fantasy to add to the pile.

After getting cleaned up and dressed he played World of Warcraft until his dad came home. He went down to the kitchen to greet him, seeing him frowning at the receipt from the drugstore. Panic instantly flared up inside of him, but his dad just looked up at him.

“Chaffing, huh?”

“Oh God, we are not having this conversation.”

“I was a teenager too, y’know.”

“Please stop talking.”

**OoOoOoO**

It had gotten to a point where he couldn’t jerk off without at the very least rubbing a finger against his hole. It was the thing he’d become addicted to, coming from just stroking his dick never feeling as good without the other possibility there.

He couldn’t help it some nights though, his dad would be home or Scott would be spending the night and he was _loud_ when he stuffed his fingers up his ass. Stiles had tried biting his fist or his pillow or anything, but nothing seemed to completely stop him from moaning and writhing around. It just felt so _good_ , his body couldn’t contain it.

Of course that wasn’t the only thing he had issues with while fingering himself. He could never imagine a girl during it. Jerking off? Sure. Lydia Martin or any of the other pretty girls at school could be giving him a hand job or sucking him off. But fingering him? He just couldn’t see it.

It wasn’t like he hadn't tried imagining it. He had been so close a few weeks ago, right before winter break had started. Lydia had asked him if he had any gum and he had nodded, giving her a piece of his favorite mint mojito like it was no big deal. She told him thanks and he had spent the entire class watching as she chewed it, bringing a finger into her mouth and stretching it out before bringing it back in.

He had gone home with the worst hard on, falling onto his bed and grabbing a bottle of lube from his stash as quickly as he could. Stiles had been on his knees, the image of Lydia’s perfectly manicured fingernails and soft hands right into view before he froze up, quickly imagining a random blob of a person spreading Stiles on their fingers.

Afterward he had felt like a failure, so close to imagining Lydia Martin giving him what he wanted, but still so far away.

He still liked girls and he still liked Lydia and there wasn’t a doubt in his mind that he always would. But the idea of a guy holding him down and spreading him open before fucking into him just made something inside of him turn hot all over. The weight of having someone firm and muscled and heavy on top of him, of filling him up with something bigger than three or four of his fingers.

Stiles wasn’t surprised when he palmed himself through his sweatpants, feeling his erection already there. So, he liked dudes. No big deal. He’d survive. Being bi wasn’t the end of the world. But this hard on was going to be the end of the world if he didn’t do something about it.

He paused his game, placing the controller on the couch before practically running up the stairs. Or halfway running up the stairs and then walking because running with a hard on wasn’t an easy thing to do.

Finally he made it to his room, kicking the door shut behind him and going to where he kept his lube. After the first time he had fingered himself and saved up enough money afterward he had gone to the same drugstore with his game face on, purchasing every type of lube he could find (even the ones for female pleasure, but staying away from the oil-based after doing some research). Laney had raised an eyebrow at his basket (with a whole package of Reese’s on top of it like he was trying to hide what he was actually buying) before shrugging and starting to scan.

He restocked a lot and Laney was always there, letting him know when they got a new brand or type in. It had taken him a while to realize that it wasn’t anything to be embarrassed about and most people’s first thought wasn’t him using it to stick his fingers up his ass.

Like he was currently doing. School started again tomorrow and two weeks hadn’t been enough to release all the tension. Especially since for most of it he had been at his Great Aunt Agnes’ house, sharing a room with his 12 year-old cousin, Jonah, who was just now figuring out what his dick was for. Fuck, that had been a nightmare.

But now his dad was working a nightshift and Scott had wanted to get buff for lacrosse or something (the kid had asthma, Stiles didn’t know why he even tried), so it was just him and his favorite source of entertainment.

Stiles shuddered, his eyelids fluttering closed as he pressed a fourth finger inside of himself. He rarely used four, usually coming with a hand on his dick and three fingers snug inside of him. But he had time now, time and his other hand fisted in his pillow behind his head, not daring to let it go to his cock like he wanted.

The fourth finger stung in the best possible way, stretching him open and making him moan. Sometimes he thought about putting his entire hand inside of himself, but the angle was all wrong and he was too scared to actually do it. Maybe if someone else did it several years down the road when he felt more confident in his ass.

Right now he was happy to take four, fucking them inside of himself and pressing against his prostate. He arched his back off the bed slightly, his breath coming out in breathy little moans as his hand continued to tighten on the pillow. He had never come without touching his cock and he knew he was going to have to give up eventually. Stiles knew that he would have to touch himself when the fingers inside of himself brought him closer and closer to the edge but never succeeded in toppling him over. Something would just have to-

“ _Sir, we’ve found a_ –”

“Oh!” Stiles gasped, coming onto his stomach and making him shake.

He definitely hadn’t been expecting a voice coming from the police scanner he’d wired through his laptop. His dad still thought that he overheard phone conversations, but the scanner was so much easier. Nevertheless, he was kind of bummed that the first time he came untouched was because something had surprised him, what a waste.

“ _Can you repeat that_?”

“ _Uh, it’s, well,_ half _of a body._ ”

Or maybe it wasn’t a total waste. Because that definitely sounded like a fun thing to do before starting the second semester of his sophomore year.

**OoOoOoO**

“This is cruel and unusual punishment.”

“How is it punishment?” Derek laughed, rolling his shoulders and rippling the muscles of his back which was just… unfair. “You signed up for this.”

“I got guilt tripped into it,” Stiles said. “Besides, it’s December and I’m fucking cold and why would anyone sign up for this?”

“Help thy neighbor?” Derek suggested.

Stiles glared at him and Derek laughed again and it was like the strangest role reversal in the world.

The first semester of his junior year was over and things had been surprisingly calm. Things had actually been calm since before the summer started. After the whole Jackson being a Kanima thing ended nothing else had really happened. Life was calm in Beacon Hills and Stiles couldn’t see it changing anytime soon.

It was currently getting dangerously close to his curfew though and he was still trying to get his portion of work done. Derek had decided to tear down and then rebuild a house on his family’s land and everyone was lending a hand. Scott and the other betas had already left a few hours ago, but Stiles was still painting the living room like he had been for most of the day.

“You could help, y’know,” Stiles suggested, looking at Derek who was watching him from the only piece of furniture, a couch in the middle of the room.

“This is your job, Stiles,” Derek said. “I’m not going to take it away from you. Besides you’re almost done.”

“Doesn’t stop the fact that it’s fucking cold since you don’t have heating installed and paint fumes are giving me a headache,” Stiles said, sniffling his nose as if on cue.

Derek didn’t say anything, just giving him a surprised look before leaving the room. Stiles couldn’t blame him, probably not wanting to spend time with him ranting on and on. It was his own fault, having woken up late and arriving at the house hours behind everyone else. He was cranky and tired and Derek lived here and probably didn’t want to listen to him complain about everything.

Or maybe not.

Something heavy came down on his shoulders over his hoody and he looked down, seeing Derek’s legendary leather jacket resting there. He felt himself flush, looking from the jacket to Derek. Derek who was currently strapping a dust mask around Stiles' face, the elastic snapping on the back of his head.

“You can return the jacket tomorrow,” Derek said before sitting back down on the couch, a book in his hand. “But get any paint on it and you’ll regret it.”

He stared at Derek in somewhat disbelief, not really used to the caring gestures (minus the threat), when Derek made a shooing motion with his hand, making him get back to work. More time passed and eventually he was done, the living room now a dark forest green (that did not make him think of a certain alpha werewolf’s eyes, no, not at all).

“I’m heading out,” Stiles said after washing off his supplies and making sure that he really hadn’t gotten any paint on Derek’s jacket.

“See you tomorrow,” Derek said, not even looking up from his book.

Stiles nodded awkwardly before heading out. The whole Derek thing had started a week within meeting him (more like the second he saw him strutting toward him and Scott in the preserve, telling them to get off private property) and hadn’t really gone away. The Lydia thing had disappeared completely and had been replaced by Derek. Derek with his green eyes and his dark hair and stubble and stupid muscles and cheekbones.

Apparently he had a thing for crushing on people who were unattainable. But it was different this time. He hadn’t even known Lydia while he had infatuated over her, but he knew Derek. He knew his favorite color and his middle name and what kind of cake his dad used to make for him on his birthday. They had had talks and he had never seen Derek date anyone and Stiles hadn’t even kissed anyone, so, he had hopes.

Hopes that always started with something like Derek giving him his jacket and ended with something like Derek not giving him a real goodbye.

It didn’t really matter though, because Derek’s jacket was still on him and it smelled like him, all spices and warm earth and something that he could only call _man_. Every time he smelled anything like it it made his head spin and heart ache and Derek knew what he did to him, he had to. But he never acted on anything or even told Stiles to stop.

Stiles entered the quiet and dark house, knowing that his dad had probably just come home from a long shift and was more than likely passed out and dead to the world. He took a quick shower before heading into his room, dropping Derek’s jacket on his pillow before collapsing onto his bed and inhaling.

He was so freaking weird sometimes, but if werewolves were allowed to have a smell thing then so was he. Except maybe werewolves didn’t get hard off of certain smells, but he had never really asked Scott that much detail before.

But here he was, his face in Derek Hale’s jacket and his hands slowly taking off his boxers and t-shirt. He wondered if Derek would know what he had done when he got the jacket back. What if he didn’t say anything? What if he did say something? What if he said something and it was that Stiles was a sick fuck?

Pushing that last one from his mind, Stiles sat up, opening up his favorite drawer and grabbing a bottle of his favorite lube. He was tired sure, but this was a golden opportunity and he wasn’t going to let it pass.

He started by teasing himself more than usual because Derek probably would. Derek would probably kiss his neck and press his fingers against his hole, maybe mutter a few words in his ear and make him squirm around. His cock was already getting hard, brushing against the sheets as he lightly pressed his fingers against himself, his ass moving back and trying to get more. Finally, he gave in, slipping two fingers inside and groaning into Derek’s jacket, the smell of the older man filling his nose.

Stiles started to rut against the sheets, imagining the weight Derek would have against him, the solid feel of his muscles, the heat of his skin. He was so far gone, so ridiculously crazy about Derek that he couldn’t even think about anyone else. He never thought that it would be possible, for his mind to block out anyone but Derek, but it had.

And with his fingers pressing inside of him and his cock brushing against the sheets and his face in the leather that smelled like Derek, he felt pathetic and desperate all at once. He knew that if he ever got the chance (the _opportunity_ ) to be with Derek that he’d ask him to fuck him within half a second. He wanted the older man inside of him and around him and all over him until his senses were so consumed that he was completely senseless.

He came like that, groaning Derek’s name desperately, his hand clutching the jacket. It took a while for him to get down from his high, feeling sad and embarrassed and knowing that there was no way Derek wouldn’t smell him on the jacket. Stiles sat up, reaching for the tissues just as he looked through the window, see two red eyes glowing back at him.

And then he promptly yelped, falling off his bed and into a heap on the floor.

He heard his window slide open and he reached around quickly for his boxers or anything to cover himself with. Eventually he managed to find a pair of sweatpants, slipping them on while sitting down (not an easy task) before standing up. Derek was standing there, looking about a thousand different emotions Stiles couldn’t place.

“You’re a voyeur,” Stiles said before Derek could get a word in, pointing accusingly.

“You were moaning my name and smelling my jacket while jerking off,” Derek said.

Okay, they were equally at fault here.

There was about two seconds of awkward staring before Derek was striding toward him, taking his face in his hands and kissing him. Stiles froze up, his hands in the air and his eyes wide, before Derek wrapped an arm around his waist and pulled him closer and then he just sank into it. He opened his mouth, winding his arms around the older man. Derek’s mouth found his neck and he was so close to begging that it wasn’t even funny.

“You’re 16,” Derek said, biting at a spot under his jaw.

“Acute observation.”

“You’re illegal, Stiles.”

“Life on the wild side, right?”

“No,” Derek said, pressing their foreheads together. “And your dad’s about to wake up and check on you.”

“ _Shit_ ,” Stiles cursed, all but pushing Derek off of him. “Okay, we’re continuing this later, so we can talk.”

“Nothing to talk about, you’re 16.”

“And you’re the biggest killjoy and I don’t know why I like you so much.”

Derek just grinned, the bastard, before leaving out of his window. Well, at least he left the jacket.

**OoOoOoO**

“Uh, Stiles,” Scott said softly once Mr. Yukimura had turned his back to write on the board.

“Yeah buddy?” Stiles asked.

“You kind of, uh, smell.”

“Gee, thanks.”

“No, you smell like…” he trailed off, clearly trying to find the right word.

Stiles just continued to take notes, allowing Scott all the time he needed to –

“Like a vagina?” Scott whispered, his voice filled with confusion.

That made Stiles almost fall out of his chair because there was no way in hell he smelled anything like any lady parts. Like Derek parts (through jeans and no actual skin-to-skin contact)? Hell yes. Like his hands and various amounts of lube and come? Yes. Lady parts? Not likely.

“Are you and Derek going through a bad time or something?”

“What? No,” Stiles said quickly. “We’re great, the make out session we had last night was –”

“Mr. Stilinski, Mr. McCall,” Mr. Yukimura said, giving them both pointed looks. “I’m here for your benefit and I’d appreciate it if you didn’t disrupt my class.”

They both gave quick apologies before Mr. Yukimura turned his back again. And Stiles turned to Scott again. He was about to question further when he shifted slightly in his seat, the skin between his ass wet and sensitive and he couldn’t help but let out a small moan. That was… new, very new.

Scott looked back at him, a pained expression on his face and Stiles tried to give him a thumb’s up or something, but a wave of pleasure overcame him. He squeezed his eyes shut, hands tightening on the edge of his desk as his mouth fell open in a louder moan. Snickers were heard around him and he couldn’t even find the energy to care, slowly raising his hand.

“Yes, Mr. Stilinski?”

“Bathroom,” he practically moaned out, his face heating up at the suppressed laughs around him.

“Go ahead,” Mr. Yukimura said, confusion evident in his voice.

Stiles was out of the room as quickly as possible, practically running down the halls as he headed to the boys’ bathroom. He entered the handicapped stall, locking it before pressing his hands against the tile wall, inhaling deeply.

It was the witch, it had to be the witch. She had passed through a week ago, not meaning any harm at all, just to give them all gifts. Glinda had practically shown up, wishing them all long happy lives and sharing advice to each of them. For Stiles she had just patted a hand on his cheek, saying that his gift would last for a week.

And there was no way this couldn’t be his gift. He got that she had the best intentions at heart, but this was just way too much for him to handle. Well, at school anyway.

Stiles unfastened his jeans, pulling them down with his boxers and letting out a loud moan at the feeling of his ass against the cool air of the bathroom. He reached a shaky hand behind him, gently touching at his hole and nearly going to his knees at the feeling.

His ass was wet and slick and so sensitive he felt like he could come within two more touches. Stiles’ cock was already hard, more than ready to come. He felt like he was going to fall apart and he wanted nothing more than to get in his Jeep and drive to Derek’s and beg the older man to just take him already (but his 18th birthday was still three months away and that man was so fucking stubborn).

Slowly, he reached his hand back again, fingers gently prodding until his face was pressed against the tile wall, completely uncaring of the grossness of the boys’ bathroom. He slipped the tip of a finger inside of him and the pleasure flared up, not making him come, just making him sweatier and harder and wetter. The lubricant dripped out of his ass, slicking his balls and traveling to the inside of his thighs.

He moaned, feeling desperate as he shoved three fingers inside of himself, his knees buckling and a choked-out cry escaping from his lips. If anyone came into the bathroom or even walked past the door he’d be done for, but he couldn’t care. All he could do was focus on his own pleasure, taking whatever he wanted from himself.

Four fingers were pressed inside and the tip of his thumb was wriggling in beside them. More slick made its way out of him, covering his thighs and making wet sounds echo in the stall. He was panting now, sweat covering his skin and tears prickling at his eyes. He couldn’t believe he was actually doing this, but he was so wet and he opened up so well and he needed to get whatever spell she had used. Stiles needed this later for after he was 18 so that Derek could fuck him like this.

That thought let a whimper escape from his mouth, a heat burst into his stomach. He just kept pressing his hand inside of himself, the angle doing nothing for his wrist, but everything for the feelings being brought out of him. Soon he was shaking and rutting against the bathroom wall, hygiene be damned. The breath was being stolen right out of him and all he could do was gasp and shake until it all became too much. He came untouched, letting out a strangled moan and almost collapsing onto the tile floor.

Instead of collapsing, Stiles slowly took his hand out of himself, still surprised he’d actually done that, before slowly sitting down on the toilet.

Well that had been an… interesting experience. One that he was going to have to repeat several times that week. Maybe even once in front of Derek, hopefully it would get him so riled up that he might do something scandalous like hold his hand while he fisted himself.

Even though knowing Derek and his extremely good restraint, he probably wouldn’t even let it go that far.

**OoOoOoO**

“How’s the dorm?”

“It’s, y’know, a dorm,” Stiles said, squinting at the room. “My roommate is a big Playboy fan.”

“Oh?” Derek chuckled. “How’s that working out?”

“Fine, I guess,” Stiles shrugged despite Derek not being able to see him. “If it makes him happy, I don’t care.”

There was silence from the other line and Stiles twitched uncomfortably on his dorm bed. It was his second week of college and they still hadn’t slept together. Derek had found out that his younger sister was still alive a week before his 18th birthday and had promptly went to South America to find her. That had been in early April and now it was early September.

“I miss you,” Stiles said, picking at a loose strand on his shirt.

“I miss you too,” Derek sighed. “And I’m very grateful that you haven’t broken up with me.”

“Why would I do that?”

“College, new beginnings, I broke a promise I made to you.”

“For good reason,” Stiles said. “I wasn’t going to postpone you finding your sister just because I wanted to get laid. And screw the college new beginnings shit. Even though there are a few good-looking guys in my classes.”

He heard a growl from the other end and he grinned, knowing that it was more playful than anything. He could never cheat on Derek, never dump him or leave him, because he cared for him way too much.

“Your classes done for the day?” Derek asked.

“Yeah and my roommate is staying at his girlfriend’s tonight.”

Stiles knew what he was proposing and Derek did as well. There were a few beats of silence before Derek spoke again. “Well, I’m alone in my hotel room.”

“Huh, so we’re both alone in rooms with beds, how strange,” Stiles said, walking across the room to his bottom desk drawer.

“It is a strange coincidence,” Derek said. “What are you getting?”

“Lube and uh, something else.”

“Oh?” Derek asked, interest sounding piqued. “What else?”

“Something I bought recently,” Stiles said, taking out a bottle of lube and a vibrator from his desk drawer.

He had only used it twice, both times at home and coming so hard he was afraid he would wake up the neighbors. Now that he lived in a dorm there was no doubt people would hear him, but it was the afternoon and most people would be in class or eating lunch. He hoped anyway.

“Tell me what it is, Stiles.”

“A vibrator,” Stiles finally said, dropping it on the bed along with the lube before lying himself down. “It’s not that big, like two of my fingers.”

“You like it?”

“Yeah,” Stiles nodded. “I’d like having you inside of me more though.”

Derek groaned from the other line and Stiles felt his mouth twitch up into a grin, loving that he could render Derek speechless sometimes.

“I always want you inside of me, Derek,” Stiles said, yanking his pants and boxers down his legs as he pressed his phone between his cheek and shoulder. “No matter what I’m doing it’s like I miss you inside of me despite you never even being there.”

“You can be so poetic,” Derek said, the noises of clothes shuffling coming clearly over the phone. “Touch yourself for me.”

“Mmkay,” Stiles mumbled, pouring lube onto his hand before encircling his cock and giving it a few strokes.

Derek never failed to get him hard fast. Every aspect of Derek turned him on, from his voice to his body to just thinking about him. He was like his personal Viagra and once he started thinking about Derek in any kind of sexual way (which was most of the time when they were apart) he couldn’t stop until he was coming.

Now was no exception, especially with the older man on the other line, talking him through it.

“Finger yourself,” Derek said, grunting slightly and letting Stiles know exactly what he was doing.

Stiles just moaned, closing his eyes and picturing Derek fisting his cock in his hotel room. He always imagined Derek taking it slow, wanting it to last as long as possible. He thought of the older man stretched out on the bedspread, talking into the phone and thrusting up into his fist, imagining that it was Stiles. Much like Stiles was imagining that it was Derek opening himself up right now.

“Wish this was you,” Stiles breathed, his fingers curling in just the right place, making him keen. “I want you so bad, Derek.”

“Me too,” Derek groaned. “Fuck, what are you doing?”

“Two fingers,” he said, his free hand grabbing for the vibrator. “About to put the vibe in.”

“Shit, that’s hot,” Derek said. “God, I wanna see you.”

He felt himself heat up even more at that. He could do that, take a picture of himself and send it to Derek. What would he even think though? Would he like it? Save it as his wallpaper or something? That probably wouldn’t be a good idea since anyone would be able to pick up his phone and see Stiles in a way that he only wanted Derek to see.

Pushing all thoughts of pictures from his mind, Stiles grabbed the vibrator, slicking it up before pressing it inside. He hissed at the cold metal, his head tilting back against his pillow. It always felt so cold and foreign at first, but soon it would warm up.

“Is it in?” Derek asked from the other line.

“Yeah,” Stiles said.

“How’s it feel?”

“Cold,” Stiles said automatically. “And it’s… good. Feels good to have something that’s not me inside of me.”

Derek groaned and Stiles wanted to ask him if he was close. He wanted to ask him when the last time he had jerked off had been, but he knew that Derek was getting off on Stiles talking more than he would if he was the one talking.

“Imagine me being inside of you,” Derek said.

“I do,” Stiles said, moving the toy in and out of himself. “All the time. I want it so bad.”

“How bad?”

“More than most things,” Stiles said, gasping as it hit his prostate. “ _Fuck_ , Der, I miss you.”

“I know, baby,” Derek groaned.

He couldn’t wait any longer, turning on the vibe and letting out an honest to God whine. They were both panting now, not even able to say anything anymore. He heard Derek let out his name like a curse before there was just soft breathing from him. Stiles pressed the toy against his prostate, wanting to come more than anything and getting his wish in just a few seconds.

Coming without touching his cock was going to be one of those impressive talents that would never see the light of any of his résumés.

Stiles took his phone from the crook of his shoulder, deciding to put all insecurities aside, and open the camera app. He pointing it to his lower half, taking a shot of his come covered stomach and softening dick and spread thighs.

After sending it to Derek he brought the phone back to his ear, hearing Derek saying his name.

“I’m here,” he said, taking the vibe out and dropping it on the bed next to him. “You should be getting a text soon.”

Soon translated into a second because he soon heard Derek let out a low, “ _Fuck_.”

**OoOoOoO**

“Just, right there, no, to the _left_.”

“Stiles.”

“No, you’re not finding it, it’s to the _left_ , Derek.”

“I know, that’s what you said.”

“Then why aren’t you pressing against it?”

Derek took his fingers out of him which was the last thing he wanted to do. His eyebrows knitted together and Stiles curled an ankle around his bicep, urging him forward.

“I thought that it would be a good thing to be your first,” Derek said, moving up to lie on top of him. “I wouldn’t have anyone to compete with. I guess I was wrong.”

“I am amazing at fingering myself,” Stiles said. “I’ve had five years of practice.”

“And I’m very grateful for that video you sent me,” Derek said, kissing him.

Their lips moved against each other’s for a while. Stiles felt a bit of worry overcome him then. What if he had just spent so long making this all up in his mind? They had been together for years and were only just now having sex. Yeah that meant that what they had was a lot more than physical activity, but what if the physical stuff didn’t work out? What if they weren’t compatible like he’d thought?

“Stop worrying,” Derek said, pressing kisses against his jaw and making his stubble tickle his skin. “Just don’t talk, okay? I know you know how to make yourself feel good. But let me do this, okay? Let me make you feel good in a way that’s different from you touching yourself.”

And Stiles really couldn’t say no to that, especially since this was finally happening. He had finished his freshman year and was back in Beacon Hills, Derek just arriving himself a few days earlier. They were in the new Hale house, in Derek’s ridiculous canopy bed, and he was about to have the first time that Disney Princesses probably dreamed about. He really shouldn’t complain because Derek couldn’t find his prostate within the first five seconds.

Derek kissed down his chest, hands placed firmly on his hips to keep them from moving. He completely bypassed his cock, going to his inner thighs instead. Stiles tried to squirm in Derek’s hold as the older man bit at his thighs, but his grip on him was firm. He could still make noises though and he would, knowing that Derek definitely got off on how loud he was.

His thighs were spread even more and Stiles couldn’t even have a second to react before Derek’s mouth was on his hole. His brain short-circuited or just stopped working completely, his mouth opening in a noiseless moan and his entire body ceasing up.

And then Derek was coaxing him with his lips and tongue and he was melting into a mindless puddle. He gripped the pillow behind his head, thrusting as best as he could against Derek’s mouth despite his hold on him. He just wanted more, more of Derek’s mouth and hot, wet tongue, opening him up. It was more sensation than he could have imagined and it was only amplified by Derek using the lube from earlier to slip two fingers inside of him, making him clench up and moan.

Okay, Derek didn’t need to find his prostate automatically to make him feel good, he got that now.

“Don’t stop,” he said, not even knowing which act he was talking about. He just knew that he didn’t want Derek to ever stop touching him.

Derek continued too, curling his fingers (broader than Stiles’ own and filling him up easier) and tracing his rim with his tongue. He was shaking and his cock was red and so ready for Derek. He wanted Derek inside of him years ago and the fact that he had him here, _finally_ , was driving him crazy.

“ _Please_ , Derek,” he groaned, moving his ass back and spreading his legs even more. “Want- Want you inside.”

“I am,” Derek said, curling his fingers as he took his mouth away.

Well, Derek had definitely found it now. Stiles bucked back against his hand, gasping as Derek tapped against his prostate. Spots were dancing in front of his eyes and his cock gave a valiant twitch and Stiles gripped the base of himself tightly, not wanting to come. “Der, please.”

“You want it that bad?” Derek asked, two fingers turning into three.

Stiles nodded frantically. He had wanted it since he was 14 and confused out of his mind when it came to liking guys, but he had still wanted it, somewhere in his mind. He had wanted it even more when he had gotten to know Derek and want Derek and love Derek.

“More than anything,” Stiles said. “Please, Derek. I need you, inside, right now.”

“God you’re bossy,” Derek said, taking his fingers out before slicking himself up.

Derek’s lips were on his before he could even think and he eagerly kissed, taking the tongue that was pushed into his mouth. It was a distraction, he knew that, a distraction from Derek’s cock pressed inside of him. He moaned at the fullness of it all, Derek’s cock better than anything and everything else.

“Gonna knot you next time,” Derek said, his voice like a promise.

Stiles could only nod, already knowing all about Derek’s werewolf dick and all of the advantages of it. He wanted it all, but figured that he could have one normal fucking before more than likely wanting Derek’s knot every time.

He knew that he’d want Derek’s cock every time though. It was hot and hard and filling him better than anything else could ever hope to. There were a few moments of adjustments for both of them, filled with Derek pressing soft kisses to his skin and Stiles focusing on breathing until he was nodding. Derek thrust inside of him, shortly and slowly at first before going for deeper and faster thrusts.

Whatever problems Derek’s fingers had had with finding his prostate at first, his cock did not share. It hit it almost dead-on with every thrust, making him a moaning mess within seconds. He wasn’t going to last and he knew that Derek wouldn’t either.

Stiles wrapped his arms around Derek’s neck, hiking his legs up for a deeper thrust. A few more and he was coming, hands gripping skin and crying out, not even caring about anyone hearing. Derek buried his face in his neck, giving a muffled groan before coming inside of him.

“Derek?” Stiles said once he had found his voice.

“Yeah?”

“Let’s do that again.”

**Author's Note:**

> This is the most self-indulgent thing I have ever written in my entire life, I'm tempted to gift it to myself. Basically I just wanted a fic of Stiles fingering himself for the first time and it turned into this. Title from a T-Swift song (literally none of you are surprised by this point), except I changed the lyric from "we" to "I".
> 
> [My tumblr](http://erinpond.tumblr.com), in case you have any questions (or just want to talk about bottom!Stiles, because I'm always game for that).
> 
> Thanks for reading! :))


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